Electronic effects in asymmetric hydroboration

To determine whether electronic effects are operative in asymmetric hydroboration, a series of para-substituted 2-aryl-1-propenes were prepared and reacted with four asymmetric borane reagents. A significant correlation between the electronic nature of the para-substituent and the degree of asymmetr...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 46; pp. 8339 - 8342
Main Authors Garner, Charles M., Chiang, Shirley, Nething, Matthew, Monestel, Robert
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 11.11.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
RELATIVE RATES
9-BORABICYCLO<3.3.1>NONANE
REPRESENTATIVE HETEROCYCLIC OLEFINS
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Summary:To determine whether electronic effects are operative in asymmetric hydroboration, a series of para-substituted 2-aryl-1-propenes were prepared and reacted with four asymmetric borane reagents. A significant correlation between the electronic nature of the para-substituent and the degree of asymmetric induction was observed only for a chloroborane–ether complex, not for any of several simple alkylboranes. A quantitative analysis of the relative reactivities is also given. The asymmetric hydroboration of a series of para-substituted 1-arylpropenes with four chiral boranes was studied. A significant electronic effect was observed with a chloroborane–ether complex, but not for any simple alkylboranes.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02013-0